Megan Murphy used to write reports on new pharmaceuticals for sophisticated investors.

Yet last month, she sat in her Northwest Portland home sweating over the wording of a brief invitation for a political fundraiser.

"I was incredibly nervous," she says.

Murphy, 47, is a lifelong Democrat. Two of her uncles are Teamsters. Before spending a decade on Wall Street, she interned for then-U.S Rep. Ron Wyden (D-Ore.). When she moved home to Portland from the East Coast, she canvassed for Ted Wheeler, a Democrat, and, in 2016, voted for Hillary Clinton—and Gov. Kate Brown.

But last month, Murphy invited 50 people to her home to meet the candidate she's supporting for governor in the November election. It was not the incumbent, Brown, a Democrat, but her Republican opponent, state Rep. Knute Buehler (R-Bend).

"Brown's been pretty disappointing to me," Murphy says. "She's unable to make hard decisions because that would disappoint her labor-union supporters. There's just a general lack of vision and lack of strategy about how to make things better."

Murphy's rejection of a Democratic incumbent offers a window into the perplexing situation in which Brown finds herself.

Brown's path to re-election should be easy. She's running in one of the bluest states in the country. The economy is strong and unemployment remains at record lows. A volcanic hatred of President Donald Trump energizes her Democratic backers.

And since becoming governor in 2015, Brown, 58, has boosted the minimum wage, pushed through groundbreaking environmental legislation and even mollified business interests with a $5.3 billion transportation funding package. The state's largest company, Nike, is a big supporter. She's been free from personal scandal. And her temperament is ideally suited to retail politics.

"She's warm, accessible and very real," says Maura Roche, a lobbyist and friend of Brown's for nearly 30 years. "She's just so down to earth that it's easy for all kinds of people to relate to her."

Just one problem: Despite all the advantages Brown possesses, Oregonians don't much like her.

Pollsters say her "negatives"—the number of people who won't vote for her—are persistently high. They're significantly higher, says pollster John Horvick of DHM Research in Portland, than they are for other statewide Democrats, such as U.S. Sens. Ron Wyden and Jeff Merkley, and higher even than the numbers for former Gov. John Kitzhaber before the scandal that led to his resignation in 2015.

"In focus groups, we ask, 'What comes to mind when you think of Kate Brown?'" Horvick says. "They really struggle to come up with anything. What is the policy she's pushed through or an argument she's taken to the voters? They can't say. She's just nondescript to them."

Brown acknowledges she's got a problem.

"I'm not sure everyone understands my style," she says. "Why I do what I do, how I do what I do."

Most of Oregon's congressional delegation crowded into the room to protest the appointment of U.S. Supreme Court nominee Brett Kavanaugh. Oregon's two U.S. senators—Wyden and Merkley—were there, but it was Brown who spoke first.

She used the opportunity to smack Buehler.

"I'm disappointed my opponent has been silent since Kavanaugh was nominated in July," Brown said. (A week later, Buehler asked for an FBI investigation of Kavanaugh.)

Combat does not come naturally to Brown. A hiker, cyclist and equestrienne, she'd rather be riding her horse, Tazo, than filming hit pieces.

Brown grew up in Minnesota, moved to Portland for law school at Lewis & Clark College in 1982 and never left. When she speaks, the round O's of her home state roll out, giving her the folksy sound of Frances McDormand in the movie Fargo.

A family and juvenile-rights lawyer, Brown entered the Legislature in 1991, rising to become Senate majority leader. She won election as secretary of state in 2008. Brown served in that post until becoming governor upon Kitzhaber's resignation amid an influence-peddling scandal in February 2015.

Because of the unusual circumstances of her ascension to the governor's office, Brown is running statewide for the third time in six years.

She won re-election as secretary of state in 2012 (defeating Buehler, a first-time candidate). Then, in 2016, she ran to serve the balance of Kitzhaber's term, easily defeating Republican Bud Pierce, a Salem oncologist.

Over the past month, WW has spoken to Democratic voters who say they are abandoning Brown. During those conversations, three themes emerge repeatedly: Oregon's frayed social safety net, a sense of lawlessness on the streets, and a failed educational system.

"I've worked on so many campaigns and bond measures for Democrats," says Maura White, a lifelong Northeast Portland resident. "My friends are going to kill me when they find out I'm voting for Knute."

White, 55, has spent her career in social services and says she agrees with Brown on most issues—but, she says, under Democratic control, Portland's safety net no longer works.

"This is a big switch for me," White says, "but I feel like letting people sleep on the streets is not compassionate—it's negligent."

As the head of the business association in the Hollywood neighborhood, White says she's seeing storefronts shutter—she mentions Realty Trust and the bicycle shop Velo Cult, although it's unclear whether sidewalk squalor was a factor in those closures.

"I just feel like change needs to happen," White says. "We have camping and open drug-dealing all over the place. A lot of people who have been in government—like Kate Brown—aren't doing anything about it."

She notes that Buehler supported tightening the state's prescription drug monitoring program, which has contributed to a decline in opioid-related deaths, while Brown signed new laws decriminalizing street drugs.

Housing and public safety are primarily the responsibility of Portland city government, with Multnomah County handling human services and sharing the response to homelessness with City Hall. But when things go bad, people look to the top for leadership—in this case, the state's chief executive, Brown.

The governor, who represented Southeast Portland as a legislator, says she knows people like White are unhappy.

"The federal government has basically ripped the rug out from under the state's feet," Brown says. "That's why I've consistently been focused on this issue since 2015, unlike some folks who only focus on it when they are running for office."

There's no question voters in Portland are disgruntled. For 26 years, the City Auditor's Office surveyed thousands of residents about their assessment of and satisfaction with city services.

From 2012 to 2016, for instance, the livability rating dropped from 79 percent to 63 percent, the lowest level ever recorded. The city's response: It stopped conducting the survey. (The auditor says the decision was purely financial.)

Horvick says DHM's polling shows homelessness is the top issue for Portland voters—and they don't necessarily know or care that responsibility for it lies with city government.

"It's hard for her to defend what people see on the streets," Horvick says.

Multnomah County Library. (Abby Gordon)

The most basic question pollsters ask voters is whether the state is moving in the right direction or the wrong direction. Skye Whitaker says Oregon is going the wrong way.

Whitaker, a bartender, has been pouring beers and mixing drinks in the heart of downtown Portland for 14 years.

A lifelong Democrat, Whitaker, 36, is a sometime volunteer for the one of the city's most overtly progressive groups, the Community Alliance of Tenants. She's a big fan of Chloe Eudaly, arguably Portland's most liberal city commissioner. She says she voted for U.S. Sen. Bernie Sanders (I-Vt.) for president in the 2016 primary and for Hillary Clinton in the general election

But in the November governor's race, Whitaker says, she'll vote for Buehler. The explanation, she says, can be distilled to two words: "pervasive lawlessness."

Maybe it was the young man who threw a chair and motioned as if he were pulling a gun on her in her bar in March. Maybe it was the addicts who regularly shoot up in the bar's restroom. Or the frequent sight of ambulances, police cars and fire trucks hauling overdosing patrons from the Multnomah County Central Library.

"People who threaten me or do drugs in our bathroom seem to have more rights than I do," Whitaker says. "Property taxes go up every year, but there seem to be fewer services. It's bad, and I just don't feel [Mayor] Ted Wheeler or Kate Brown is doing anything about it."

Whitaker says she knows the city, not the state, is responsible for policing Portland's streets. But she draws a connection between the state's inadequate provision of mental health services and its dysfunctional foster system, on the one hand, and the frequent chaos downtown on the other.

"I feel like Brown tackles only the issues that generate positive PR," Whitaker says. "I feel she's ignoring what's going on on Portland's streets because administering some tough love or taking action on homelessness could reflect badly on her. So she's ignoring the issue and passing the buck."

Brown's heard it before—that she's too nice to make hard decisions.

She rejects that criticism.

She's fired several agency directors and the officials responsible for foster care. And she says she's repeatedly bucked unions: She supported the Trans-Pacific Partnership, a controversial trade proposal; refused to support to the $10 billion Jordan Cove liquefied natural gas project in Southern Oregon; and decided to call a special session earlier this year to extend a tax break to certain small businesses.

"That made my base grumpy," Brown says.

Oregon Gov. Kate Brown speaks to press at the scene of the Eagle Creek Fire on Sept. 6. (Thomas Teal)

Megan Murphy, who held the fundraiser for Buehler in the Northwest Portland hills last month, says Brown lost her on one fundamental issue: public pensions.

Murphy points to a letter that Katy Durant, former chairwoman of the Oregon Investment Council, wrote to Brown in December 2016. Durant raised alarms about the increasing cost of funding pensions through the Public Employee Retirement System and the effect it would have on public services, calling the system an approaching "train wreck."

"So what did Brown do?" Murphy asks. "She formed a committee that wrote a report and did nothing. Her unwillingness to address PERS and the position of Oregon schools compared to the rest of the country is pretty shameful."

John Tapogna, president of the consulting firm ECONorthwest, says Brown has done something: She pushed legislation in 2017 that will allow local governments to begin reducing the $22 billion unfunded liability of the state pension system.

The problem, Tapogna says, is that any significant improvements from that legislation lie far in the future. In the meantime, he adds, Brown has done little to reduce costs. That means much of the increase in tax receipts from the booming economy has gone straight into retiree pensions.

"Whoever is going to be governor next is going to have to think much more expansively about PERS," Tapogna says. "If they don't, that will spell trouble for the state's reputation and economic growth."

Brown says she's tackling the issue. Although she's depended on the financial support of public employee unions her entire career, in union bargaining, she persuaded most state employees to begin paying part of the cost of their own pensions.

There's a close linkage, of course, between the overhang of pension obligations and another hot-button issue for many disaffected voters: K-12 education. Oregon class sizes remain high, and the school year is still among the nation's shortest, despite a 23 percent increase in K-12 education funding over the past four years.

Brown says she's made progress.

"We've been able to expand access to pre-K and sustain funding for it despite opposition in the Legislature," she says. "We've been able to improve high school graduation rates. I think 2017 was the biggest improvement since we started keeping track."

But Oregon's graduation rate remains stubbornly low: 47th in the nation. And the State Board of Education, whose members Brown appoints, voted recently to loosen attendance requirements for high school seniors.

That vote infuriated education advocates such as Lisa Zuniga, a Portland Public Schools parent. Zuniga notes Brown's platform calls for a longer school year, yet she's just allowed her board to move in the opposite direction.

"I don't feel a sense of urgency from Gov. Brown," Zuniga says. "I think given our lower ranking, she should have declared a state of emergency rather than lowering the bar."

Gov. Kate Brown at Pride 2017. (Office of the governor)

Brown belongs to one of the nation's most exclusive clubs: She's one of just two Democratic women governors in the nation. (Four women governors are Republicans.)

Many of Brown's supporters say sexism is a big part of why people question her leadership style—and it helps explain why her poll numbers are weak.

Labor Commissioner-elect Val Hoyle says she thinks Brown doesn't get a fair shake because of her gender.

"She's held to a different standard than male candidates," says Hoyle. "When John Kitzhaber would sit down and negotiate with business and labor leaders to keep measures off the ballot, people would say, 'Oh my gosh, what a leader he is!' When she did it earlier this year"—getting Nike and labor to agree to a deal on ballot measures—"people said she was being anti-democratic."

Hoyle says the sexism extends to the way the press and others talk about Brown: "Look at the way she's described as 'petite' or 'friendly.' The words people use are very gender-biased and not the same they use to describe male politicians."

Horvick, the pollster, agrees with Hoyle that people view Brown differently because she's a woman—and maybe also because she is bisexual. (She is the nation's first openly bisexual governor.)

Brown says the paucity of women governors around the country speaks volumes. "That tells me it is still extremely challenging," Brown says, "for voters to see women in these executive leadership positions."

Criticism of her on a whole host of issues, she says, feels to her like an issue of style, rather than substance.

Unlike many male politicians, she avoids confrontation and bold proclamations. "I try to work with people in a way that doesn't burn bridges even if I don't get what I want," Brown says. "Nobody can argue with the fact that I'm GSD—'getting stuff done.'"

That "stuff," she says, includes expanded funding for the Oregon Health Plan, an aggressive increase in the minimum wage, family medical leave and a first-of-its-kind worker-scheduling bill. Those are bread-and-butter Democratic issues that pleased Brown's base.

Environmentalists cheer her accomplishments, as well. Doug Moore, executive director of the Oregon League of Conservation Voters, says Brown has been more engaged and more effective on environmental issues than was Kitzhaber.

That's high praise, because the conventional narrative pegged Brown's predecessor as an environmental champion.

"Kitzhaber knew what he wanted to do, but he was hard to engage with," Moore says. "She's just better—I'd argue the best governor on environmental issues in a generation."

And business groups cheered when Brown secured the largest transportation funding package in Oregon history last year—$5.3 billion—overcoming significant obstacles. Jana Jarvis, a lobbyist for the Oregon Trucking Associations, says the governor deserves praise for that. "It wouldn't have happened without her office pulling things together," Jarvis says.

But there's no love for Brown among Republicans, despite the transportation package and other attempts on her part to cross the aisle.

"If you look back to when Kitzhaber and [former Gov. Ted] Kulongoski were running, they'd get some support from Republicans," Horvick says. "That's just not happening anymore."

Republicans haven't won an Oregon governor's race since 1982. When Dennis Richardson defeated Labor Commissioner Brad Avakian in the 2016 secretary of state's race, he became the first Republican to win statewide office in Oregon since 2002.

A socially conservative Mormon from rural Oregon's ability to defeat a liberal Democrat from the metro area gives some Republicans optimism about Buehler's chances.

A supporter of same-sex marriage and one of just three Republicans in the House to support a successful gun control bill in 2018, Buehler is more moderate than Richardson—and his best chance of winning appears to lie in appealing to disaffected moderate Democrats and the ballooning number of nonaffiliated voters (see above).

Brown knows that. That's why she slammed Buehler at the recent Planned Parenthood event, and why she and her backers refuse to concede Buehler's claim that he's pro-choice.

She has to convince skeptics Buehler is dangerous. Because being Kate Brown isn't enough.

"We started tracking her negatives a year ago," a Salem lobbyist says. "They've never gone down. That means people have passed judgment on her. She cannot run ads and tell people about all her successes, because they won't believe it. That means her only choice is to kick the shit out of Knute."